Citation: Liu Shizhao, Abudu Rexit·Abulikemu. A Simple, Mild, Efficient and Metal-Free Synthesis Method of Disulfides[J]. Chemistry, ;2019, 82(3): 270-274. shu

A Simple, Mild, Efficient and Metal-Free Synthesis Method of Disulfides

  • Corresponding author: Abudu Rexit·Abulikemu, aarexit@xjnu.edu.cn
  • Received Date: 15 October 2018
    Accepted Date: 16 November 2018

  • In this paper, thiophenols or mercaptans were self-coupled to form bisulfide in the presence of tribromophenone with 95% ethanol as solvent, which provided a mild, simple, green and metal-free synthesis method after traditional methods. A variety of thiophenols and mercaptans were investigated under the optimum reaction conditions. It was found that aromatic hydrocarbons containing electron withdrawing groups could obtain higher yields than that with electron-withdrawing groups, and the reaction time was also shorter. At the same time, the substrates of aliphatic and heterocyclic compounds also had relatively higher yields in this reaction.
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    1. [1]

      L Bischoff, C David, L Martin et al. J. Org. Chem., 1997, 62:4848~4850. 

    2. [2]

      F. Hosseinpoor, H Golchoubian. Catal. Lett., 2006, 111:165~168.

    3. [3]

      T Tsuboi, Y Takaguchi, S Tsuboi. Bull. Chem. Soc. Jpn., 2008, 81:361~368. 

    4. [4]

      K D Lee, G Saito, J A Swanson. Adv. Drug. Delivery. Rev., 2003, 55:199~215. 

    5. [5]

    6. [6]

      R J Crem-lyn. An Introduction to Organosulfur Chemistry, Wiley & Sons, New York, 1996.

    7. [7]

       

    8. [8]

    9. [9]

      M Oba, K Tanaka, K Nishiyama et al. J. Org. Chem., 2011, 76:4173~4177. 

    10. [10]

      S Thurow, V A Pereira, D M Martinez et al. Tetrahed. Lett., 2011, 52:640~643. 

    11. [11]

      K Bahrami, MM Khodaei, V Shakibaian et al. Phosphorus Sulfur Silicon Relat. Elem., 2013, 188:981~988. 

    12. [12]

      M Hayashi, K Okunaga, S Nishida et al. Tetrahed. Lett., 2010, 51:6734~6736. 

    13. [13]

      C Tidei, M Piroddi, F Galli et al. Tetrahed. Lett., 2012, 53:232~234 

    14. [14]

      F Rajabi, T Kakeshpour, M R Saidi. Catal. Commun., 2013, 40:13~17. 

    15. [15]

      W L Dong, G Y Huang, Z M Li et al. Phosphorus Sulfur Silicon Relat. Elem., 2009, 184:2058~2065. 

    16. [16]

      M Joshaghani, A R Khosropour, H Jafary. Phosphorus Sulfur Silicon Relat. Elem., 2005, 180:117~123. 

    17. [17]

      S S Bayraq, A Nikseresht, I Khosravi. Phosphorus Sulfur Silicon Relat. Elem., 2013, 188:1236~1243. 

    18. [18]

      I Yavari, A A Rounaqi, L Moradi. Phosphorus Sulfur Silicon Relat. Elem., 2006, 181:2659~2662. 

    19. [19]

      H Xiao, J Chen, M Liu. Phosphorus Sulfur Silicon Relat. Elem., 2009, 184:2553:2559. 

    20. [20]

      U Pathak, L K Pandey, S Mathur. Synth. Commun., 2009, 39:2923~2927. 

    21. [21]

      C A S Regino, D E Richardson. Inorg. Chim. Acta., 2007, 360, 3971~3977.

    22. [22]

      G W Kabalka, M S Reddy, M L Yao. Tetrahed. Lett., 2009, 50:7340~7342. 

    23. [23]

      S Ghammamy, M Tajbakhsh. J. Sulfur Chem., 2005, 26:145~148. 

    24. [24]

      M Soleiman-Beigi, M Hemmati. Appl. Organometal. Chem., 2013, 27:734~736. 

    25. [25]

      N Iranpoor, H Firouzabadi, D Khalili. Tetrahed. Lett., 2012, 53:6913~6915. 

    26. [26]

      E M Hamed, H Doai, C K McLaughlin et al. J. Am. Chem. Soc., 2006, 128:6595~6604. 

    27. [27]

      D Sengupta, B Basu. Tetrahed. Lett., 2013, 54:2277~2281. 

    28. [28]

      A Talla, B Driessen. Adv. Synth. Catal., 2016, 46:2180~2186.

    29. [29]

      Y Y Liu, H Wang, C P Wang et al. RSC Adv., 2013, 3:21369~21372. 

    30. [30]

      J Luis, G Ruano, A Parra. Green Chem., 2008, 10:706~711. 

    31. [31]

      S Samanta, S Ray, A B Ghosh et al. RSC Adv., 2016, 47:39356~39363.

  • 加载中
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